Chlorosuccinimide → HCID 136337819, compound

HRID 1187997Notes

Reaction equation

HRID 1187997 reaction equation
[OH:1][N:2]=[CH:3][C:4]1[CH:16]=[CH:15][C:7]([C:8]([NH:10][CH:11]=[N:12][O:13][CH3:14])=[O:9])=[C:6]([CH3:17])[CH:5]=1.ClN1C(=O)CCC1=O.[Cl:26][C:27]1[CH:28]=[C:29]([C:37]([C:39]([F:42])([F:41])[F:40])=[CH2:38])[CH:30]=[C:31]([C:33]([F:36])([F:35])[F:34])[CH:32]=1.C(=O)([O-])O.[K+]>COCCOC.O>[Cl:26][C:27]1[CH:28]=[C:29]([C:37]2([C:39]([F:40])([F:41])[F:42])[O:1][N:2]=[C:3]([C:4]3[CH:16]=[CH:15][C:7]([C:8]([NH:10][CH:11]=[N:12][O:13][CH3:14])=[O:9])=[C:6]([CH3:17])[CH:5]=3)[CH2:38]2)[CH:30]=[C:31]([C:33]([F:34])([F:35])[F:36])[CH:32]=1

Participants

8

Reactant 4

HCID 31398ChlorosuccinimideHCID 516893Potassium BicarbonateHCID 86654468HCID 86654468, compoundHCID 136337818HCID 136337818, compound

Product 1

HCID 136337819HCID 136337819, compoundYield 11.7%

Reagents, catalysts & solvents 3

HCID 962WaterCatalystHCID 962WaterSolventHCID 80711,2-DimethoxyethaneSolvent

Conditions

Temperature
70 °C

Procedure

In a solution of 81 mg of 4-hydroxyiminomethyl-N-(methoxyiminomethyl)-2-methyl benzoic acid amide in 10 ml of 1,2-dimethoxyethane, 60 mg of N-chlorosuccinimide was added, and stirred at 70° C. for 45 minutes. Then, the reaction mixture was left and cooled to room temperature, and then 60 mg of 3-chloro-5-trifluoromethyl-1-(1-trifluoromethylethenyl)benzene, 40 mg of potassium hydrogen carbonate and 3 drops of water were added, and continued to stir at room temperature further for 15 hours. After the completion of the reaction, the reaction mixture was poured in 10 mL of water, and extracted with ethyl acetate (15 mL×2). The combined organic phases were dehydrated with and dried over saturated sodium chloride aqueous solution and then anhydrous magnesium sulfate, and the solvent was distilled off under reduced pressure. The residue was purified with silica gel column chromatography that were eluated with ethyl acetate-hexane (gradient of 1:5 to 1:3) to obtain 13 mg of the aimed product as colorless resinous substance.

Workup

  1. waitThen, the reaction mixture was left
  2. temperaturecooled to room temperature
  3. stirringto stir at room temperature further for 15 hours
  4. customAfter the completion of the reaction
  5. extractionextracted with ethyl acetate (15 mL×2)
  6. dry with materialdried over saturated sodium chloride aqueous solution
  7. distillationanhydrous magnesium sulfate, and the solvent was distilled off under reduced pressure
  8. customThe residue was purified with silica gel column chromatography that

Sources & evidence

ORD record
ord-5f0bbdc5755940bd9c6d054a7c627e2a
Source dataset
uspto-grants-2014_03
Patent number
US08673951B2

Reaction notes

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